This post’s title is a direct quote from a member of an old work team, talking about his role as risk-identifier, gadfly, pessimist and occasional nay-sayer. I wrote most of it in 2009, but it turns out to be entirely applicable 15 years later.
I recall many a project-management-of-people class touching on the idea of pessimist as a useful team role, to the point of designating someone to pick apart all the reasons a solution might not work. I assume there’s some organizational behavior research behind this recurring idea, too – there’s almost always some form of psychology at the heart of any simplified management truism.
That notion isn’t unique to projects or even “management”; deBono’s thinking hats thing, for instance, includes a hat of “critical judgment”, which I like to think of as the hat of angst and risk aversion, the hat of speaking the team’s unspoken fears.
In any case.
I don’t believe optimism is foolish. It can be, but it’s just as likely to be a result of experience and trust. You get through one cluster of a problem, and you begin to see paths through others. It’s not a failure to see problems so much as a belief that they’ll get solved.
Where I see pessimism being truly helpful, though, is not in the popular domain of risk (sure, that’s handy, but you can get to risks from a lot of different directions, and getting too critical or analytical can paralyze a group). It’s the pessimist’s willingness to be an iconoclast, to stand against something. As the world’s come to recognize the difficulty of taking a stand, we’re better understanding the need to make that safe. Standing against is still taking a stand. Even a wobbling uh, guys, I don’t think this is going to work stance is a way of injecting dissent into a group conversation.
And it turns out you can cultivate that. While people are evolving the idea of “psychological safety” to include the breadth of different inclusion and safety efforts needed to make it safe for someone to show up as their full self, the origin of the phrase is in making it safe to take stands on a team.
That’s the whole idea everyone gets from the Asch experiment, right? One black sheep, and suddenly it turns out sheep are like My Little Pony and come in all colors.
Dissent, used well, is how we get a whole picture as a team.
That is – sometimes groups don’t even notice they’re falling into consensus too easily. It takes a pessimist – someone brave or smart enough not to fear conflict – to throw up the 40 point card in planning poker and point out how much the group doesn’t understand yet. Just one voice of dissent from an apparent agreement, and it turns out the issue is much more complex, and is actually being understood in several different ways. That diversity of thought contributes to teams outperforming individuals, and it’s often the grumpy pessimist who kicks that off.
As change leaders, it’s particularly important for us to not just listen to, but actually cultivate, the pessimists. Knowing the effort it takes to speak up, we need to create safe opportunities for people to do so. We need to see all aspects of response to change in order to design well.